Structure Database (LMSD)

Common Name
Rotundone
Systematic Name
(3S,5R,8S)-3,8-dimethyl-5-prop-1-en-2-yl-3,4,5,6,7,8-hexahydro-2H-azulen-1-one
Synonyms
LM ID
LMPR0103410008
Formula
C15H22O
Exact Mass
Calculate m/z
218.167065
Status
Curated
Show lipids differing only in stereochemistry/bond geometry

Classification

Category
Main Class
Sub Class
Level 4 Class
Prenol Lipids [PR]
Isoprenoids [PR01]
C15 isoprenoids (sesquiterpenes) [PR0103]
Guaiane sesquiterpenoids [PR010341]

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Cyperus rotundus (#512623)
Magnoliopsida (#3398)
Sesquiterpenoids from the essential oil of Cyperus rotundus,
Tetrahedron Letts, 1967
Vitis vinifera (#29760)
Magnoliopsida (#3398)
From wine to pepper: rotundone, an obscure sesquiterpene, is a potent spicy aroma compound.,
J Agric Food Chem, 2008
Pubmed ID: 18461961

String Representations

InChiKey (Click to copy)
NUWMTBMCSQWPDG-SDDRHHMPSA-N
InChi (Click to copy)
InChI=1S/C15H22O/c1-9(2)12-6-5-10(3)15-13(8-12)11(4)7-14(15)16/h10-12H,1,5-8H2,2-4H3/t10-,11-,12+/m0/s1
SMILES (Click to copy)
C1C[C@H](C)C2C(=O)C[C@H](C)C=2C[C@@H]1C(=C)C

Other Databases

CHEBI ID
191710
PubChem CID
5321003

Calculated Physicochemical Properties

Heavy Atoms 16
Rings 2
Aromatic Rings
Rotatable Bonds 1
Van der Waals Molecular Volume 244.21
Topological Polar Surface Area 17.07
Hydrogen Bond Donors
Hydrogen Bond Acceptors 1
logP 3.90
Molar Refractivity 67.13

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Created at
25th Dec 2022
Updated at
25th Dec 2022